The 16 Greatest Upsets in Heavyweight Boxing History

Today I want to compare and rate the greatest upsets in heavyweight history. The criteria here is how big the upset was when it happened. Ali is on here a couple of times, and to be truthful, knowing what we know now, we could probably relegate those to not being upset. But, let’s face it; they don’t call him “The Greatest” for nothing.

16) Michael Bentt KO 1 Tommy Morrison

Four months before this fight, Tommy Morrison had beaten George Foreman to claim the WBO heavyweight title, and a fight was looming with Lennox Lewis. Bentt, on the other hand, was a 10-1 underdog and had lost his pro debut to Jerry Jones. The competition he had faced did not indicate that he would deal with Morrison. Bentt was a great amateur fighter but had not lived up to expectations so far in his career. However, that all changed on this night as he didn’t just beat Morrison; he knocked him out in the first round!

RIP Tommy Morrison vs Bentt 1st rd. KO

15) James J. Corbett KO 21 John L. Sullivan

Sullivan was 38-0-1 and was the self-proclaimed baddest SOB around. He had offered a purse of $25,000 and a $10,000 side bet winner-take-all, and Corbett and his manager took him up on it. Corbett boxed the entire fight beautifully and slowly wore Sullivan out until round 21 when an exhausted Sullivan was beaten senseless by Corbett, who became the second gloved Heavyweight Champion in history.

One More Round – James J Corbett vs John L Sullivan

14) Gene Tunney UD Jack Dempsey I

Dempsey and Babe Ruth were the most popular athletes of the roaring ’20s, and Dempsey took that fame to heart and fought seldom. Unfortunately, it caught up to him in this fight. This is one of those fights where hindsight makes this not look like it’s not so big of an upset. Dempsey had not fought in a little over three years before this, and Tunney is an all-time great fighter. Tunney controlled the fight easily, winning in front of over 120,000 fans.

Gene Tunney -vs- Jack Dempsey I 1926 World Heavyweight Championship (Restored Full Fight))

13) Andy Ruiz Jr KO 7 Anthony Joshua

Ruiz had been a solid pro coming into this fight, and most fight fans thought that Joshua was the best heavyweight in the world (he’s not). However, Ruiz didn’t just land a single punch to win; he repeatedly knocked Joshua down. On this night, he was the best fighter; no luck was involved.

HIGHLIGHTS | Anthony Joshua vs. Andy Ruiz Jr.

12) Corrie Sanders KO 2 Wladimir Klitschko

Sanders was a relative unknown heading into this fight, and Klitschko looked like a man who had the skill could dominate the heavyweight division for the next decade. Instead, Sanders exposed Wladimir’s most significant weakness in front of the world, his chin.

Wladimir Klitschko vs Corrie Sanders 2003 03 08 full fight

11) Ken Norton SD 12 Muhammad Ali I

In this fight, Ali was ranked number one and Norton number six. Norton had no standout victories, and nobody gave him much of a chance. The surprising thing here is that he got the decision! Norton broke Ali’s jaw during the fight and was the definite winner.

Muhammad Ali vs Ken Norton The Fight Ali Had His Jaw Broken | Boxing Classic Highlights 4K Ultra HD

10) Muhammad Ali KO 8 George Foreman

Ali was 32 years old, and on the downside of his career, at least that’s what most people thought. Foreman was seemingly invincible, knocking out Joe Frazier in two rounds. It seemed the same fate would await Ali. But, instead, Ali employed a rope a dope tactic to tire out Foreman and eventually knocked out Foreman in the eighth round of a classic and unforgettable battle.

Muhammad Ali vs George Foreman (Highlights) The Rumble In The Jungle

9) Cassius Clay KO 7 Sonny Liston I

Once again, Ali faced what was considered an invincible opponent, and once again, Ali showed everybody that nobody was invincible. Ali may have won the fight mentally before it began, as he acted like a crazy man in the lead-up to the fight. However, during the fight, he showed speed no heavyweight has ever shown, even today.

Ali vs Liston 1 | How Ali SHOOK UP the World – Breakdown

8) Hasim Rahman KO5 Lennox Lewis

Lewis was coming off a dominant performance against the tough David Tua and looked to be at the height of his powers. Rahman was a good fighter with a strong punch but was widely seen as a soon-to-be knockout victim. Lewis came into the fight at his highest weight up to that time and got flattened by a stunning right hand near the end of the fifth round.

JEFF JACKSON BOXING HIGHLIGHTS | Lennox Lewis vs Hasim Rahman I (UPSET)

7) Leon Spinks SD 15 Muhammad Ali

Spinks was in just his eighth pro bout, and just two fights before had struggled to get a draw with Scott LeDoux in a fight most thought LeDoux had won. Ali was older and slower, but he had enough to beat the tough Earnie Shavers just a few months before. Ali tried a little rope a dope against Spinks, but Spinks was too strong and kept coming after Ali. As Ali would say after the fight, Spinks was relentless on the attack.

Muhammad Ali vs Leon Spinks “Legendary Night” Highlights HD #ElTerribleProduction

6) Michael Spinks UD 15 Larry Holmes

No Light Heavyweight Champion had ever beaten the Heavyweight Champion. To make the upset even better, Holmes was just one win away from Rocky Marciano’s 49-0. In three months, Spinks gained over twenty pounds under the guidance of nutritionist Mackie Shilstone. Whatever Shilstone did at the training table and in their workouts worked as Spinks constantly beat Holmes to the punch to win a close but deserved decision.

Larry Holmes vs Michael Spinks l (Highlights)

5) James Braddock UD 15 Max Baer

The bout was held at the Madison Square Garden Bowl, nicknamed “The Graveyard of Champions” because no reigning champion had ever successfully defended his title there. And to the surprise of most in attendance, the Graveyard of Champions would bury another one. Baer was seemingly disinterested in fighting on this night, and Braddock took full advantage to win a close but just decision.

JEFF JACKSON BOXING HIGHLIGHTS | James Braddock vs Max Baer (CINDERELLA MAN)

4) Evander Holyfield KO 11 Mike Tyson I

People forget that Tyson was on a roll in this fight, and Holyfield looked old in his last four fights while winning just two of them. At the opening of betting, Tyson was a 25-1 favorite, which was bet down to 10-1 by fight time. Holyfield, in the end, was just the stronger fighter physically, and, more importantly, mentally.

Mike Tyson (USA) vs Evander Holyfield (USA) | KNOCKOUT, BOXING fight, HD

3) Oliver McCall KO 2 Lennox Lewis

McCall was a hot and cold heavyweight who had some good wins but also some bad losses. Lewis seemed almost unbeatable going into this fight. He was young, strong, and fast. But, in the end, younger, stronger, and faster was not enough because McCall landed a huge right hand that stopped Lewis in the second round.

Lennox Lewis vs Oliver McCall 1994 WBC title

2) Max Schmeling KO 11 Joe Louis

Max was the former Heavyweight Champion of the World, but the odds were still over 10-1 against him as he faced the young “Brown Bomber” who had knocked out former Champions Primo Carnera and Max Baer. Schmeling was considered old and over the hill, but he said he saw a weakness in Louis, and he did! He dropped Louis in the 4th round and could barely miss with his right hand afterward, stopping Louis in the 12th.

Joe Louis vs Max Schmeling – I + II Highlights in High Quality & in Color

1) James Douglas KO 10 Mike Tyson

This fight is number one, and it’s not even close! Tyson was a 42-1 favorite and had been quickly dispatching everything that got in his way, while “Buster” had quit against Tony Tucker, and most questioned how much heart Douglas had. On one February night in Tokyo, Japan, Buster Douglas was special and dominated Tyson for most of the fight, finally leaving Tyson on the canvas searching for his mouthpiece, a beaten fighter.

Buster Douglas shocks the world with 10th-round KO of Mike Tyson | ESPN Archives